Bis(benzoyl-acetonato)bis-(1,3-di-4-pyridyl-propane)manganese(II).

In the title compound, [Mn(C(10)H(9)O(2))(2)(C(13)H(14)N(2))(2)], the Mn(II) ion lies on a crystallographic inversion center and has a slightly distorted octa-hedral coordination environment. Weak π-π stacking inter-actions, with centroid-centroid distances of 3.862 (2) and 3.887 (5) Å, and significant C-H⋯π inter-actions help to stabilize the crystal structure. The atoms of the unique terminal 4-pyridine-propane group are disordered over two sites, the ratio of refined occpancies being 0.712 (7):0.288 (7).

Related literature

For the β-diketone group, see: Yoshida et al. (1999 ▶). For factors influencing structures and applications, see: Ghosh et al. (2004 ▶). For the 1-benzoyl­acetone ligand, see: Han & Zhou (2008 ▶); Bučar & Meštrović (2003 ▶); Meštrović et al. (2004 ▶). For 1,3-bis(4-pyridyl)propane, see: Carlucci et al. (2002 ▶); Han et al. (2007 ▶).

Experimental

Crystal data

[Mn(C10H9O2)2(C13H14N2)2]

M = 773.81

Triclinic,

a = 9.771 (2) Å

b = 10.269 (2) Å

c = 10.485 (2) Å

α = 79.84 (3)°

β = 77.68 (3)°

γ = 89.45 (3)°

V = 1011.3 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.37 mm−1

T = 298 K

0.43 × 0.27 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.886, T max = 0.949

9996 measured reflections

4583 independent reflections

2625 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.131

S = 1.11

4583 reflections

279 parameters

22 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.85 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009891/lh2780sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009891/lh2780Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C10H9O2)2(C13H14N2)2]	Z = 1
Mr = 773.81	F(000) = 407
Triclinic, P1	Dx = 1.271 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.771 (2) Å	Cell parameters from 9996 reflections
b = 10.269 (2) Å	θ = 3.1–27.4°
c = 10.485 (2) Å	µ = 0.37 mm−1
α = 79.84 (3)°	T = 298 K
β = 77.68 (3)°	Block, yellow
γ = 89.45 (3)°	0.43 × 0.27 × 0.14 mm
V = 1011.3 (3) Å3

Rigaku R-AXIS RAPID diffractometer	4583 independent reflections
Radiation source: fine-focus sealed tube	2625 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 0 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −12→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.886, Tmax = 0.949	l = −13→13
9996 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0212P)2 + 0.8043P] where P = (Fo2 + 2Fc2)/3
4583 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.44 e Å−3
22 restraints	Δρmin = −0.85 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Mn1	0.5000	0.5000	0.5000	0.0515 (2)
O1	0.5977 (2)	0.4870 (2)	0.2980 (2)	0.0588 (6)
O2	0.4772 (2)	0.70055 (19)	0.4153 (2)	0.0583 (6)
N1	0.7142 (3)	0.5550 (2)	0.5435 (3)	0.0554 (7)
C1	0.6164 (3)	0.5749 (3)	0.1942 (3)	0.0561 (8)
C2	0.5774 (3)	0.7069 (3)	0.1891 (3)	0.0543 (8)
H2A	0.5942	0.7611	0.1060	0.065*
C3	0.5159 (3)	0.7642 (3)	0.2973 (3)	0.0497 (7)
C4	0.4914 (3)	0.9105 (3)	0.2811 (3)	0.0512 (7)
C5	0.4131 (4)	0.9594 (3)	0.3870 (4)	0.0663 (9)
H5A	0.3739	0.9010	0.4644	0.080*
C6	0.3917 (4)	1.0938 (4)	0.3806 (4)	0.0818 (11)
H6A	0.3375	1.1247	0.4528	0.098*
C7	0.4501 (5)	1.1811 (4)	0.2680 (5)	0.0850 (12)
H7A	0.4377	1.2715	0.2640	0.102*
C8	0.5270 (4)	1.1340 (4)	0.1614 (4)	0.0819 (12)
H8A	0.5656	1.1929	0.0841	0.098*
C9	0.5481 (3)	0.9997 (3)	0.1673 (4)	0.0649 (9)
H9A	0.6009	0.9693	0.0942	0.078*
C10	0.6872 (5)	0.5313 (4)	0.0665 (3)	0.0889 (13)
H10A	0.7800	0.5030	0.0723	0.133*
H10B	0.6927	0.6039	−0.0061	0.133*
H10C	0.6340	0.4591	0.0522	0.133*
C11	0.7529 (4)	0.5049 (3)	0.6567 (3)	0.0638 (9)
H11A	0.6941	0.4413	0.7173	0.077*
C12	0.8743 (4)	0.5418 (4)	0.6887 (4)	0.0677 (9)
H12A	0.8959	0.5029	0.7688	0.081*
C13	0.9645 (3)	0.6367 (4)	0.6023 (4)	0.0631 (9)
C14	0.9256 (3)	0.6873 (3)	0.4842 (4)	0.0655 (9)
H14A	0.9830	0.7503	0.4215	0.079*
C15	0.8025 (3)	0.6449 (3)	0.4595 (3)	0.0610 (8)
H15A	0.7793	0.6812	0.3793	0.073*
C16	1.0969 (4)	0.6845 (4)	0.6333 (4)	0.0850 (12)
H16A	1.1748	0.6787	0.5599	0.102*	0.712 (7)
H16B	1.1152	0.6272	0.7115	0.102*	0.712 (7)
C17	1.0873 (5)	0.8315 (6)	0.6584 (6)	0.0735 (18)	0.712 (7)
H17A	1.1786	0.8627	0.6649	0.088*	0.712 (7)
H17B	1.0597	0.8880	0.5843	0.088*	0.712 (7)
C18	0.9821 (5)	0.8393 (5)	0.7845 (5)	0.0715 (18)	0.712 (7)
H18A	0.8921	0.8054	0.7778	0.086*	0.712 (7)
H18B	1.0112	0.7826	0.8578	0.086*	0.712 (7)
C19	0.9642 (5)	0.9769 (5)	0.8155 (6)	0.0585 (14)	0.712 (7)
C20	0.8366 (7)	1.0339 (8)	0.8254 (7)	0.068 (2)	0.712 (7)
H20A	0.7619	0.9881	0.8099	0.082*	0.712 (7)
C21	0.8167 (10)	1.1545 (10)	0.8570 (9)	0.091 (4)	0.712 (7)
H21A	0.7279	1.1890	0.8605	0.109*	0.712 (7)
C22	1.0392 (10)	1.1755 (10)	0.8710 (12)	0.084 (3)	0.712 (7)
H22A	1.1114	1.2260	0.8848	0.101*	0.712 (7)
C23	1.0715 (6)	1.0503 (7)	0.8387 (7)	0.0711 (19)	0.712 (7)
H23A	1.1614	1.0180	0.8331	0.085*	0.712 (7)
N2	0.9127 (8)	1.2275 (7)	0.8834 (7)	0.083 (3)*	0.712 (7)
H16C	1.1545	0.7357	0.5537	0.102*	0.288 (7)
H16D	1.1497	0.6092	0.6635	0.102*	0.288 (7)
C17A	1.0611 (15)	0.7711 (11)	0.7420 (13)	0.067 (4)*	0.288 (7)
H17C	0.9851	0.7311	0.8133	0.080*	0.288 (7)
H17D	1.1421	0.7844	0.7785	0.080*	0.288 (7)
C18A	1.0178 (15)	0.9009 (11)	0.6687 (12)	0.067 (4)*	0.288 (7)
H18C	1.0926	0.9332	0.5927	0.081*	0.288 (7)
H18D	0.9355	0.8841	0.6355	0.081*	0.288 (7)
C19A	0.9859 (14)	1.0068 (12)	0.7515 (15)	0.059 (4)*	0.288 (7)
C20A	0.8553 (17)	1.0579 (18)	0.7869 (19)	0.065 (6)*	0.288 (7)
H20B	0.7773	1.0231	0.7654	0.079*	0.288 (7)
C21A	0.843 (2)	1.1620 (17)	0.855 (2)	0.054 (6)*	0.288 (7)
H21B	0.7535	1.1924	0.8812	0.064*	0.288 (7)
C22A	1.071 (2)	1.170 (2)	0.861 (3)	0.061 (6)*	0.288 (7)
H22B	1.1456	1.1995	0.8918	0.073*	0.288 (7)
C23A	1.0905 (17)	1.0689 (16)	0.7889 (16)	0.065 (6)*	0.288 (7)
H23B	1.1814	1.0408	0.7635	0.078*	0.288 (7)
N2A	0.9475 (18)	1.2239 (16)	0.8872 (17)	0.066 (5)*	0.288 (7)

	U11	U22	U33	U12	U13	U23
Mn1	0.0558 (4)	0.0467 (4)	0.0503 (4)	0.0015 (3)	−0.0082 (3)	−0.0078 (3)
O1	0.0646 (14)	0.0521 (13)	0.0569 (14)	0.0078 (11)	−0.0061 (11)	−0.0110 (11)
O2	0.0687 (14)	0.0483 (12)	0.0537 (13)	0.0068 (10)	−0.0045 (11)	−0.0088 (10)
N1	0.0563 (16)	0.0563 (16)	0.0534 (16)	0.0028 (13)	−0.0106 (13)	−0.0110 (13)
C1	0.0542 (19)	0.063 (2)	0.0501 (19)	0.0049 (16)	−0.0084 (15)	−0.0119 (16)
C2	0.0583 (19)	0.0516 (18)	0.0499 (18)	0.0080 (15)	−0.0104 (15)	−0.0028 (15)
C3	0.0432 (17)	0.0510 (17)	0.0534 (19)	−0.0011 (14)	−0.0101 (14)	−0.0055 (15)
C4	0.0473 (17)	0.0473 (17)	0.0599 (19)	0.0012 (14)	−0.0172 (15)	−0.0051 (15)
C5	0.076 (2)	0.058 (2)	0.066 (2)	0.0128 (18)	−0.0185 (19)	−0.0120 (17)
C6	0.104 (3)	0.064 (2)	0.086 (3)	0.026 (2)	−0.030 (2)	−0.026 (2)
C7	0.101 (3)	0.053 (2)	0.111 (3)	0.011 (2)	−0.041 (3)	−0.017 (2)
C8	0.087 (3)	0.052 (2)	0.099 (3)	0.000 (2)	−0.019 (2)	0.007 (2)
C9	0.063 (2)	0.055 (2)	0.072 (2)	0.0001 (16)	−0.0108 (18)	−0.0048 (17)
C10	0.119 (3)	0.082 (3)	0.059 (2)	0.014 (2)	0.003 (2)	−0.022 (2)
C11	0.069 (2)	0.061 (2)	0.059 (2)	0.0008 (17)	−0.0101 (18)	−0.0083 (17)
C12	0.071 (2)	0.075 (2)	0.064 (2)	0.015 (2)	−0.0243 (19)	−0.0189 (19)
C13	0.0507 (19)	0.073 (2)	0.074 (2)	0.0129 (17)	−0.0137 (18)	−0.036 (2)
C14	0.054 (2)	0.074 (2)	0.067 (2)	−0.0038 (17)	−0.0042 (17)	−0.0181 (18)
C15	0.060 (2)	0.066 (2)	0.055 (2)	0.0002 (17)	−0.0079 (17)	−0.0105 (17)
C16	0.060 (2)	0.101 (3)	0.110 (3)	0.016 (2)	−0.025 (2)	−0.056 (3)
C17	0.047 (3)	0.102 (5)	0.075 (4)	−0.007 (3)	−0.007 (3)	−0.030 (4)
C18	0.069 (3)	0.077 (4)	0.070 (4)	−0.005 (3)	−0.009 (3)	−0.023 (3)
C19	0.055 (3)	0.071 (3)	0.051 (3)	−0.002 (3)	−0.013 (3)	−0.011 (3)
C20	0.051 (3)	0.081 (5)	0.074 (5)	−0.003 (3)	−0.019 (3)	−0.009 (4)
C21	0.057 (5)	0.117 (8)	0.099 (6)	0.012 (4)	−0.016 (4)	−0.019 (4)
C22	0.078 (7)	0.093 (6)	0.084 (5)	−0.037 (5)	−0.017 (5)	−0.017 (4)
C23	0.049 (3)	0.096 (5)	0.070 (5)	−0.001 (3)	−0.017 (3)	−0.014 (4)
C16A	0.060 (2)	0.101 (3)	0.110 (3)	0.016 (2)	−0.025 (2)	−0.056 (3)

Mn1—O2	2.124 (2)	C15—H15A	0.9300
Mn1—O2i	2.124 (2)	C16—C17	1.576 (6)
Mn1—O1i	2.157 (2)	C16—H16A	0.9700
Mn1—O1	2.157 (2)	C16—H16B	0.9700
Mn1—N1	2.330 (3)	C17—C18	1.506 (6)
Mn1—N1i	2.330 (3)	C17—H17A	0.9700
O1—C1	1.266 (3)	C17—H17B	0.9700
O2—C3	1.273 (3)	C18—C19	1.505 (6)
N1—C15	1.333 (4)	C18—H18A	0.9700
N1—C11	1.337 (4)	C18—H18B	0.9700
C1—C2	1.400 (4)	C19—C20	1.364 (6)
C1—C10	1.511 (4)	C19—C23	1.384 (6)
C2—C3	1.390 (4)	C20—C21	1.339 (8)
C2—H2A	0.9300	C20—H20A	0.9300
C3—C4	1.505 (4)	C21—N2	1.310 (9)
C4—C5	1.377 (4)	C21—H21A	0.9300
C4—C9	1.383 (4)	C22—N2	1.331 (9)
C5—C6	1.386 (5)	C22—C23	1.403 (8)
C5—H5A	0.9300	C22—H22A	0.9300
C6—C7	1.368 (5)	C23—H23A	0.9300
C6—H6A	0.9300	C17A—C18A	1.521 (13)
C7—C8	1.368 (5)	C17A—H17C	0.9700
C7—H7A	0.9300	C17A—H17D	0.9700
C8—C9	1.385 (5)	C18A—C19A	1.498 (13)
C8—H8A	0.9300	C18A—H18C	0.9700
C9—H9A	0.9300	C18A—H18D	0.9700
C10—H10A	0.9600	C19A—C23A	1.369 (13)
C10—H10B	0.9600	C19A—C20A	1.377 (14)
C10—H10C	0.9600	C20A—C21A	1.377 (14)
C11—C12	1.374 (5)	C20A—H20B	0.9300
C11—H11A	0.9300	C21A—N2A	1.339 (15)
C12—C13	1.382 (5)	C21A—H21B	0.9300
C12—H12A	0.9300	C22A—N2A	1.322 (15)
C13—C14	1.384 (5)	C22A—C23A	1.375 (15)
C13—C16	1.506 (5)	C22A—H22B	0.9300
C14—C15	1.374 (4)	C23A—H23B	0.9300
C14—H14A	0.9300
O2—Mn1—O2i	180	C13—C14—H14A	119.9
O2—Mn1—O1i	97.35 (8)	N1—C15—C14	123.9 (3)
O2i—Mn1—O1i	82.65 (8)	N1—C15—H15A	118.1
O2—Mn1—O1	82.65 (8)	C14—C15—H15A	118.1
O2i—Mn1—O1	97.35 (8)	C13—C16—C17	112.3 (3)
O1i—Mn1—O1	180	C13—C16—H16A	109.1
O2—Mn1—N1	90.12 (9)	C17—C16—H16A	109.1
O2i—Mn1—N1	89.88 (9)	C13—C16—H16B	109.1
O1i—Mn1—N1	88.68 (9)	C17—C16—H16B	109.1
O1—Mn1—N1	91.32 (9)	H16A—C16—H16B	107.9
O2—Mn1—N1i	89.88 (9)	C18—C17—C16	110.2 (4)
O2i—Mn1—N1i	90.12 (9)	C18—C17—H17A	109.6
O1i—Mn1—N1i	91.32 (9)	C16—C17—H17A	109.6
O1—Mn1—N1i	88.68 (9)	C18—C17—H17B	109.6
N1—Mn1—N1i	180	C16—C17—H17B	109.6
C1—O1—Mn1	129.9 (2)	H17A—C17—H17B	108.1
C3—O2—Mn1	131.8 (2)	C19—C18—C17	114.0 (4)
C15—N1—C11	115.8 (3)	C19—C18—H18A	108.7
C15—N1—Mn1	121.5 (2)	C17—C18—H18A	108.7
C11—N1—Mn1	122.6 (2)	C19—C18—H18B	108.7
O1—C1—C2	125.5 (3)	C17—C18—H18B	108.7
O1—C1—C10	116.2 (3)	H18A—C18—H18B	107.6
C2—C1—C10	118.3 (3)	C20—C19—C23	116.6 (5)
C3—C2—C1	125.7 (3)	C20—C19—C18	120.1 (5)
C3—C2—H2A	117.2	C23—C19—C18	123.2 (5)
C1—C2—H2A	117.2	C21—C20—C19	121.3 (7)
O2—C3—C2	124.3 (3)	C21—C20—H20A	119.3
O2—C3—C4	114.9 (3)	C19—C20—H20A	119.3
C2—C3—C4	120.8 (3)	N2—C21—C20	125.0 (9)
C5—C4—C9	118.0 (3)	N2—C21—H21A	117.5
C5—C4—C3	118.4 (3)	C20—C21—H21A	117.5
C9—C4—C3	123.5 (3)	N2—C22—C23	124.8 (7)
C4—C5—C6	121.3 (3)	N2—C22—H22A	117.6
C4—C5—H5A	119.3	C23—C22—H22A	117.6
C6—C5—H5A	119.3	C19—C23—C22	117.3 (6)
C7—C6—C5	120.0 (4)	C19—C23—H23A	121.3
C7—C6—H6A	120.0	C22—C23—H23A	121.3
C5—C6—H6A	120.0	C21—N2—C22	114.8 (7)
C6—C7—C8	119.4 (4)	C18A—C17A—H17C	111.1
C6—C7—H7A	120.3	C18A—C17A—H17D	111.1
C8—C7—H7A	120.3	H17C—C17A—H17D	109.0
C7—C8—C9	120.7 (4)	C19A—C18A—C17A	114.2 (10)
C7—C8—H8A	119.7	C19A—C18A—H18C	108.7
C9—C8—H8A	119.7	C17A—C18A—H18C	108.7
C4—C9—C8	120.6 (4)	C19A—C18A—H18D	108.7
C4—C9—H9A	119.7	C17A—C18A—H18D	108.7
C8—C9—H9A	119.7	H18C—C18A—H18D	107.6
C1—C10—H10A	109.5	C23A—C19A—C20A	114.3 (12)
C1—C10—H10B	109.5	C23A—C19A—C18A	121.1 (12)
H10A—C10—H10B	109.5	C20A—C19A—C18A	124.4 (12)
C1—C10—H10C	109.5	C21A—C20A—C19A	118.1 (15)
H10A—C10—H10C	109.5	C21A—C20A—H20B	120.9
H10B—C10—H10C	109.5	C19A—C20A—H20B	120.9
N1—C11—C12	123.8 (3)	N2A—C21A—C20A	126.7 (16)
N1—C11—H11A	118.1	N2A—C21A—H21B	116.7
C12—C11—H11A	118.1	C20A—C21A—H21B	116.7
C11—C12—C13	120.2 (3)	N2A—C22A—C23A	120.3 (17)
C11—C12—H12A	119.9	N2A—C22A—H22B	119.9
C13—C12—H12A	119.9	C23A—C22A—H22B	119.9
C12—C13—C14	116.0 (3)	C19A—C23A—C22A	125.0 (15)
C12—C13—C16	122.8 (4)	C19A—C23A—H23B	117.5
C14—C13—C16	121.2 (4)	C22A—C23A—H23B	117.5
C15—C14—C13	120.2 (3)	C22A—N2A—C21A	115.1 (14)
C15—C14—H14A	119.9

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cg1	0.93	2.56	3.159 (4)	122
C14—H14A···Cg2ii	0.93	2.91	3.738 (5)	149
C14—H14A···Cg3ii	0.93	2.63	3.440 (9)	147
C15—H15A···Cg1	0.93	2.60	3.206 (3)	123
C20—H20A···Cg4iii	0.93	2.65	3.529 (7)	158

Mn1—O2	2.124 (2)
Mn1—O1	2.157 (2)
Mn1—N1	2.330 (3)

O2—Mn1—O2i	180
O2—Mn1—O1i	97.35 (8)
O2—Mn1—O1	82.65 (8)
O1i—Mn1—O1	180
O2—Mn1—N1	90.12 (9)
O1—Mn1—N1	91.32 (9)
O2—Mn1—N1i	89.88 (9)
O1—Mn1—N1i	88.68 (9)
N1—Mn1—N1i	180

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cg1	0.93	2.56	3.159 (4)	122
C14—H14A⋯Cg2ii	0.93	2.91	3.738 (5)	149
C14—H14A⋯Cg3ii	0.93	2.63	3.440 (9)	147
C15—H15A⋯Cg1	0.93	2.60	3.206 (3)	123
C20—H20A⋯Cg4iii	0.93	2.65	3.529 (7)	158

Symmetry codes: (ii) ; (iii) .Cg1, Cg2, Cg3 and Cg4 are the centroids of the Mn1/O1/C1–C3/O2, N2/C19–C23, N2A/C19A–C23A and C4–C9 rings, respectively.